Andrew Mason

Current Company

Descript — Founder & CEO

The Fastest Billion-Dollar Company in History

Andrew Mason launched Groupon in November 2008 from a Chicago office, and within 16 months the company had reached $1 billion in revenue — faster than any company in history. The concept was simple: aggregate local buying power to negotiate group discounts with restaurants, spas, and retailers, then split the savings between consumers and the platform. At its peak, Groupon had 150 million subscribers and was turning down a $6 billion acquisition offer from Google.

The trajectory was also one of the most dramatic rises and falls in tech history. Groupon went public in 2011 at a $13 billion valuation, but the daily deals model proved difficult to sustain. Merchant quality declined, customer retention dropped, and copycats flooded the market. Mason was fired as CEO in February 2013, and he responded with a self-deprecating memo that became one of the most famous exit letters in corporate history.

A Quieter Second Act in AI Tools

After Groupon, Mason founded Descript, an audio and video editing platform powered by AI that lets users edit media as easily as editing a text document. Descript's breakthrough feature — the ability to edit audio by editing its transcript — made podcast and video production accessible to creators without professional editing skills. The company raised over $100 million in venture funding and became a default tool for podcasters and video creators.

Mason's second act reflects a founder who learned from the excesses of hypergrowth. Where Groupon scaled at all costs, Descript has grown methodically, focused on product quality and genuine utility rather than viral acquisition. Mason rarely discusses Groupon publicly, but his journey — from the fastest billion-dollar company to a public firing to a successful second startup — is one of the most instructive founder narratives in modern tech.